Identification and characterization of a welwitindolinone alkaloid biosynthetic gene cluster in the stigonematalean cyanobacterium Hapalosiphon welwitschii

ChemBioChem

Volumn 15, Issue 5, 2014, Pages 665-669

  Hillwig, Matthew L ^a   Fuhrman, Heather A ^a   Ittiamornkul, Kuljira ^a   Sevco, Tyler J ^a   Kwak, Daniel H ^a   Liu, Xinyu ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

alkaloids; biosynthesis; cyanobacteria; evolution; gene clusters

Indexed keywords

ALKALOID DERIVATIVE; AMBIGUINE; ISOTHIOCYANIC ACID; PYROPHOSPHATE; UNCLASSIFIED DRUG; WELWITINDOLINONE; INDOLE ALKALOID; N-METHYLWELWITINDOLINONE C ISOTHIOCYANATE;

AMPLICON; ARTICLE; BIOSYNTHESIS; COMPARATIVE STUDY; CYANOBACTERIUM; DRUG IDENTIFICATION; DRUG STRUCTURE; ENZYME ACTIVE SITE; ESCHERICHIA COLI; GENE CLUSTER; HAPALOSIPHON WELWITSCHII; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; OXIDATION; PRIORITY JOURNAL; TRANSPOSON; BACTERIAL GENE; CHEMISTRY; ENZYMOLOGY; GENETICS; METABOLISM; MULTIGENE FAMILY;

BIOSYNTHETIC PATHWAYS; CYANOBACTERIA; GENES, BACTERIAL; INDOLE ALKALOIDS; MULTIGENE FAMILY;

EID: 84896403588     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201300794     Document Type: Article

References (28)

1. K. Stratmann, R. E. Moore, R. Bonjouklian, J. B. Deeter, G. M. L. Patterson, S. Shaffer, C. D. Smith, T. A. Smitka, J. Am. Chem. Soc. 1994, 116, 9935.
2. C. D. Smith, J. T. Zilfou, K. Stratmann, G. M. L. Patterson, R. E. Moore, Mol. Pharmacol. 1995, 47, 241
3. X. Zhang, C. D. Smith, Mol. Pharmacol. 1996, 49, 288.
4. J. I. Jimenez, U. Huber, R. E. Moore, G. M. L. Patterson, J. Nat. Prod. 1999, 62, 569.
5. P. S. Baran, J. M. Richter, J. Am. Chem. Soc. 2005, 127, 15394
6. S. E. Reisman, J. M. Ready, A. Hasuoka, C. J. Smith, J. L. Wood, J. Am. Chem. Soc. 2006, 128, 1448
7. P. S. Baran, T. J. Maimone, J. M. Richter, Nature 2007, 446, 404
8. J. M. Richter, Y. Ishihara, T. Masuda, B. W. Whitefield, T. Llamas, A. Pohjakallio, P. S. Baran, J. Am. Chem. Soc. 2008, 130, 17938
9. V. Bhat, K. M. Allan, V. H. Rawal, J. Am. Chem. Soc. 2011, 133, 5798
10. A. D. Huters, K. W. Quasdorf, E. D. Styduhar, N. K. Garg, J. Am. Chem. Soc. 2011, 133, 15797
11. K. W. Quasdorf, A. D. Huters, M. W. Lodewyk, D. J. Tantillo, N. K. Garg, J. Am. Chem. Soc. 2012, 134, 1396
12. K. M. Allan, K. Kobayashi, V. H. Rawal, J. Am. Chem. Soc. 2012, 134, 1392
13. E. D. Styduhar, A. D. Huters, N. A. Weires, N. K. Garg, Angew. Chem. Int. Ed. 2013, 52, 12422
14. Angew. Chem. 2013, 125, 12648.
15. M. L. Hillwig, Q. Zhu, X. Liu, ACS Chem. Biol. 2014, 9, 372-377.
16. A. Raveh, S. Carmeli, J. Nat. Prod. 2007, 70, 196.
17. T. A. Smitka, R. Bonjouklian, L. Doolin, N. D. Jones, J. B. Deeter, W. Y. Yoshida, M. R. Prinsep, R. E. Moore, G. M. L. Patterson, J. Org. Chem. 1992, 57, 857.
18. Y. Wu, Q. Kang, G. Shang, P. Spiteller, B. Carroll, T.-W. Yu, W. Su, L. Bai, H. G. Floss, ChemBioChem 2011, 12, 1759
19. T. W. Giessen, A. M. von Tesmar, M. A. Marahiel, Biochemistry 2013, 52, 4274.
20. M. Pacholec, J. Tao, C. T. Walsh, Biochemistry 2005, 44, 14969
21. C. Zhang, C. Albermann, X. Fu, N. R. Peters, J. D. Chisholm, G. Zhang, E. J. Gilbert, P. G. Wang, D. L. Van Vranken, J. S. Thorson, ChemBioChem 2006, 7, 795
22. J.-H. Lee, B. Bae, M. Kuemin, B. T. Circello, W. W. Metcalf, S. K. Nair, W. A. van der Donk, Proc. Natl. Acad. Sci. USA 2010, 107, 17557.
23. F. Taura, S. Sirikantaramas, Y. Shoyama, K. Yoshikai, Y. Shoyama, S. Morimoto, FEBS Lett. 2007, 581, 2929
24. Y.-H. Chooi, Y. J. Hong, R. A. Cacho, D. J. Tantillo, Y. Tang, J. Am. Chem. Soc. 2013, 135, 16805.
25. T. P. Begley, J. Xi, C. Kinsland, S. Taylor, F. McLafferty, Curr. Opin. Chem. Biol. 1999, 3, 623
26. M. Fontecave, S. Ollagnier-de-Choudens, E. Mulliez, Chem. Rev. 2003, 103, 2149
27. E. G. Mueller, Nat. Chem. Biol. 2006, 2, 185.
28. E. Sasaki, H.-w. Liu, J. Am. Chem. Soc. 2010, 132, 15544.